WO2008122511A3 - Process for preparing 2-amino- [5-(1(s), 2-dihydroxyethyl) or - (ks) -hydroxy-2-haloethyl) ] -pyrazine derivatives by enzymatic reduction of the corresponding ketones - Google Patents

Process for preparing 2-amino- [5-(1(s), 2-dihydroxyethyl) or - (ks) -hydroxy-2-haloethyl) ] -pyrazine derivatives by enzymatic reduction of the corresponding ketones Download PDF

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Publication number
WO2008122511A3
WO2008122511A3 PCT/EP2008/053515 EP2008053515W WO2008122511A3 WO 2008122511 A3 WO2008122511 A3 WO 2008122511A3 EP 2008053515 W EP2008053515 W EP 2008053515W WO 2008122511 A3 WO2008122511 A3 WO 2008122511A3
Authority
WO
WIPO (PCT)
Prior art keywords
hydroxy
amino
haloethyl
dihydroxyethyl
preparing
Prior art date
Application number
PCT/EP2008/053515
Other languages
French (fr)
Other versions
WO2008122511A2 (en
Inventor
Steven Paul Hanlon
Hans Iding
Ernst Kupfer
Roumen Nikolaev Radinov
Lianhe Shu
Ping Wang
Original Assignee
Hoffmann La Roche
Steven Paul Hanlon
Hans Iding
Ernst Kupfer
Roumen Nikolaev Radinov
Lianhe Shu
Ping Wang
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Hoffmann La Roche, Steven Paul Hanlon, Hans Iding, Ernst Kupfer, Roumen Nikolaev Radinov, Lianhe Shu, Ping Wang filed Critical Hoffmann La Roche
Priority to EP08718198A priority Critical patent/EP2145012A2/en
Priority to CA002682304A priority patent/CA2682304A1/en
Priority to JP2010501479A priority patent/JP2010523095A/en
Publication of WO2008122511A2 publication Critical patent/WO2008122511A2/en
Publication of WO2008122511A3 publication Critical patent/WO2008122511A3/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P17/00—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
    • C12P17/10—Nitrogen as only ring hetero atom
    • C12P17/12—Nitrogen as only ring hetero atom containing a six-membered hetero ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
    • C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
    • C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D241/20—Nitrogen atoms
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Zoology (AREA)
  • Biotechnology (AREA)
  • Microbiology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Biochemistry (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)

Abstract

The present invention relates to biocatalytic asymmetric reduction for the preparation of 2-amino- [5-( l-hydroxy-2-hydroxy or halogen-ethyl) ] -pyrazine derivatives of the formula (formula I) wherein R is lower alkylcarbonyl or an amino protecting group and R1 is hydroxy or halogen. The compounds are key intermediates in the manufacture of a glucokinase activator.
PCT/EP2008/053515 2007-04-04 2008-03-26 Process for preparing 2-amino- [5-(1(s), 2-dihydroxyethyl) or - (ks) -hydroxy-2-haloethyl) ] -pyrazine derivatives by enzymatic reduction of the corresponding ketones WO2008122511A2 (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
EP08718198A EP2145012A2 (en) 2007-04-04 2008-03-26 Microbial reduction of an acetoxyketone
CA002682304A CA2682304A1 (en) 2007-04-04 2008-03-26 Microbial reduction of an acetoxyketone
JP2010501479A JP2010523095A (en) 2007-04-04 2008-03-26 Process for the preparation of 2-amino- [5- (1 (S), 2-dihydroxyethyl) or-(KS) -hydroxy-2-haloethyl)]-pyrazine derivatives by enzymatic reduction of the corresponding ketones

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP07105615 2007-04-04
EP07105615.4 2007-04-04

Publications (2)

Publication Number Publication Date
WO2008122511A2 WO2008122511A2 (en) 2008-10-16
WO2008122511A3 true WO2008122511A3 (en) 2008-11-27

Family

ID=39734157

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2008/053515 WO2008122511A2 (en) 2007-04-04 2008-03-26 Process for preparing 2-amino- [5-(1(s), 2-dihydroxyethyl) or - (ks) -hydroxy-2-haloethyl) ] -pyrazine derivatives by enzymatic reduction of the corresponding ketones

Country Status (6)

Country Link
US (1) US7727750B2 (en)
EP (1) EP2145012A2 (en)
JP (1) JP2010523095A (en)
CN (1) CN101641447A (en)
CA (1) CA2682304A1 (en)
WO (1) WO2008122511A2 (en)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20110054174A1 (en) * 2009-08-28 2011-03-03 Stephan Bachmann Process for the preparation of a glucokinase activator compound
KR20170118230A (en) 2009-12-01 2017-10-24 애브비 인코포레이티드 Novel tricyclic compounds
CN102776157B (en) * 2012-08-21 2013-09-04 尚科生物医药（上海）有限公司 Improved ketoreductase polypeptide and coding gene thereof, and cell for expressing polypeptide
IL225900A0 (en) * 2013-04-22 2014-03-31 Perrigo Api Ltd A process for the preparation of nicotine comprising the enzymatic reduction of 4-(methylamino)-1-(pyridin-3-yl)butan-1-one
CN109738506B (en) * 2019-01-10 2021-02-26 青岛大学附属医院 Research method for acetylation sites of autophagy-related proteins in mature adipocytes
CN113528588A (en) * 2021-06-15 2021-10-22 海南卓科制药有限公司 Preparation method of levocarnitine

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004052869A1 (en) * 2002-12-12 2004-06-24 F. Hoffmann-La Roche Ag 5-substituted-pyrazine or pyridine glucokinase activators

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU2003293865A1 (en) * 2002-12-12 2004-06-30 Allpresan Gesellschaft Zum Vertrieb Von Gesundheitsprodukten Fur Allergiker Mbh Stable foam cream

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004052869A1 (en) * 2002-12-12 2004-06-24 F. Hoffmann-La Roche Ag 5-substituted-pyrazine or pyridine glucokinase activators

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
KALUZNA, I.A. ET AL.: "Ketoreductases: stereoselective catalysts for the facile synthesis of chiral alcohols", TETRAHEDRON ASYMMETRY, vol. 16, no. 22, 14 November 2005 (2005-11-14), pages 3682 - 3689, XP005180018 *
WEI, Z.L. ET AL.: "Microbial transformation of 2-hydroxy and 2-acetoxy ketones with Geotrichum sp.", BIOORGANIC & MEDICINAL CHEMISTRY, vol. 8, no. 5, May 2000 (2000-05-01), pages 1129 - 1137, XP002496120 *
ZHU, D. ET AL.: "'Green' synthesis of important pharmaceutical building blocks: enzymatic access to enantiomerically pure alpha-chloroalcohols", TETRAHEDRON ASYMMETRY, vol. 16, no. 19, 3 October 2005 (2005-10-03), pages 3275 - 3278, XP005115144 *

Also Published As

Publication number Publication date
CA2682304A1 (en) 2008-10-16
WO2008122511A2 (en) 2008-10-16
JP2010523095A (en) 2010-07-15
US20080248537A1 (en) 2008-10-09
US7727750B2 (en) 2010-06-01
CN101641447A (en) 2010-02-03
EP2145012A2 (en) 2010-01-20

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